Hydrochloric Acid → HCID 21849761, compound

HRID 617778Notes

Reaction equation

Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[O:8]1[C:13]2[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](CC)([O-])=O>[CH2:10]1[CH2:9][O:8][C:13]2=[CH:14][C:15]3[S:2](=[O:4])(=[O:3])[NH:5][C:6](=[O:7])[NH:18][C:16]=3[CH:17]=[C:12]2[O:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

This compound was prepared according to the method of Girard et. al., J. Chem. Soc., Perkin I; 1979, 1043-1047, incorporated by reference herein in its entirety. To a solution of chlorosulfonyl isocyanate (5.6 g, 40.0 mmol) in nitroethane (35 ml) at -40° C. was added dropwise over five minutes a solution of 1,4-benzodioxan-6-amine (5.0 g, 33.1 mmol) in nitroethane (5 ml). The mixture was allowed to warm to 0° C. and stirred for one hour at which time anhydrous aluminum chloride was added. The mixture was warmed to 110° C. and stirred for 30 minutes (copious HCl evolution) and allowed to cool to ambient temperature before being added dropwise to a vigorously stirred ice-water (~150 g) mixture. The resulting precipitate was collected by suction filtration, washed with water and air-dried to give 4.4 g (52%) of the title compound as a light gray powder; MS: 255 m/z (M-H)-.

Workup

customThis compound was prepared
additionwas added
temperatureThe mixture was warmed to 110° C.
temperatureto cool to ambient temperature
filtrationThe resulting precipitate was collected by suction filtration
washwashed with water
customair-dried

Sources & evidence

ORD record: ord-fd782d8a8e7c4a0ca8dbbeb8c7fdb794
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952328

Reaction notes

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